Have you ever wanted to fly and knew you would never be able to? Not fall through the sky or seal yourself inside of a flying aluminum can, but just open up your door and flip physics the bird before flying off. It's something I've wanted to do for as long as I can remember. I was a huge roller coaster enthusiast growing up; I imagined myself as Superman flying to the edge of the atmosphere and orbiting the earth. I even managed to lucid dream flying on several occasions; that always made my day!

As I grew older and realized reality wasn't nearly so awesome as the comics, I had to scale it back a bit. I have had the experience of flying on commercial aircraft as well as military transports from my days as an aircraft loadmaster in the Air Force. Sadly, I couldn't manage to convince the Air Force to let me parachute down with the cargo I was dropping or I might have actually enlisted for another four years!

Even outside of the USAF, I did have a lot of airborne fun back on Earth. I've been skydiving, hang gliding, bungee jumping and even tried parasailing once. None of this, however, could ever match the sheer exhilaration of pegasi flight. Once you've been strapped to a team of winged horses and flown over a major city, none of the other stuff will ever be good enough again.

Unless your boss sends you on a job that involves staying on the ground. Then you have to do it anyway and feel really guilty about it later. The sacrifices I make for my employer...

"The answer is no, Cloud Kicker. I'm on assignment and my handler grounded me. I have to be a good boy." I leaned back on the bed and sighed.

The purple-coated, yellow-maned pegasus stretched her wings and yawned, "The longer we argue, the less time we have to fly. I also have Blossomforth outside the door and I’m not afraid to use her!"

I bolted upright in my bed. "You brought Blossomforth along!?" Shit just got real.

“Well, well, well!” A magnificent, white pegasus with a festive cerise and green striped mane and bright blue eyes. She strode into the room like the friggin’ Queen of the Nile fixing me with a disapproving glare. “You come all the way out here to Ponyville and don’t even have a second to spare for your old friends? Richard, you disappoint us!”

Four against one. I'm outflanked, outgunned, and there's no hope for support. Remember me as a Gentleman who stood calm in the face of certain doom and faced his end with courage and dignity. "How did you know even know I was here?" I sputtered, stalling for time, breaking out in a nervous sweat. Okay, maybe not so calm, courageous, or dignified.

"We stopped by Sugarcube Corner after you left and Pinkie told us what happened back there. I knew it had to be you from her description, so I flew over the roads and saw you coming in here. I fetched the rest of the girls and we've got the building surrounded." She flashed me the equine equivalent of a shit-eating grin.

I ran to the window, threw open the curtain and was greeted by the grinning face of Cloudchaser hovering mid-air. She waved and gestured toward the human flight harness which would allow me to soar through the sky along with them. With that, I held up my hands in submission. "Okay, I give up, Cloud Kicker — on two conditions. First, please get me back here safely by twenty-hundred so I can go to work, and please let me change out of my costume so the authorities won't find me dead wearing hunting clothes."

Her grin got broader. "I accept the conditions of your surrender, Stuntman. Now get the hell out of that thing and meet us outside." With that, Cloud Kicker left out of the window to let me strip out of my clothes.

Blossomforth gave me a teasing look. “I suppose you’ll be wanting me to leave too?”

Two can play at that game, Miss Blossom. “Well I’d hate to give you second thoughts about your new herd and all...”

“Mmm, touché! I’ll see you outside handsome!” Blossomforth made a show of throwing her wings open, flagged her tail at me with a wink, and took off out of the same window as Cloud Kicker.

The uncomfortable tightness in my pants told me she had come off the victor in that little sparring contest. As I stripped I noticed Cloud Kicker watching from the outside. Does she think I don’t notice? Seeing no harm in it, I decided to put on a little show for her.

*****

Equipped with flight harnesses, goggles, and towing lines, the members of the Ponyville Weather Team greeted me at the front of the dress shop before escorting me to their takeoff point. I was wrong about there being four of them it seems, they'd brought along a fifth pony named Thunderlane: A dark gray coated stallion with a silver-blue mohawk. Really great guy and has probably tucked in as many mares as eighty-percent of us at Gentleman For Mares, and even more then some. He would tow the line for Flitter as a safety precaution, and I felt a little more at ease knowing he was there.

The four pegasi mares were a pretty eclectic bunch. Blossomforth was an ex-marefriend of mine. She was (and still is) the hottest pegasus who has ever lived. She can bend herself into nearly any configuration and loves to experiment with new positions. Hell if she ever decides to quit her day job, she could write the pony sutra on sex positions. We had to call it quits when she decided to enter a herd with Cloudchaser and Thunderlane. I took it pretty hard at the time, but we're on good terms now.

Cloud Kicker, on the other hoof, is a very single-minded pegasus. There are activities that involve sex — or banging as she likes to call it — and there is the void of mundane crap that gets forced in between for the sake of survival. I do this sort of thing for a living and she even scares me sometimes.

Then there were the twins: Cloudchaser, a purple-coated mare with blue and white striped mane and tail was quite a lot of fun to hang around. We'd had our little fun in the air already so she would help Blossomforth and Cloud Kicker carry me so that I would most likely not die in the event of an emergency that put one of the three out of commission.

Ahh Flitter: almost identical to her sister Cloudchaser in appearance and absolutely nothing like her in personality. While Cloudchaser embraced the Spartan image of the pegasi, Flitter found she preferred the calm and predictable life of living on the ground, as attested to by her cutie mark depicting three dragonflies. Now living among the farm folk of Ponyville, she's also gone native to the point that she’s picked up a bit of the local accent. She wears a pink bow in her light-green mane; a look that I’m told she's favored since she was a filly. She's shy and quiet, and was relegated to the role of third-wheel like most shy mares from an early age. Cloudchaser had been trying to get her to climb out of her shell for awhile to no avail, but the Mile-High Club finally seemed to be the thing to do it. She's been looking forward to a chance to have her turn with me.

I just wasn't expecting that we would be doing this right now!

*****

After double-checking and triple-checking our harnesses we began strapping each other in. A small, green hill near the Ponyville-Canterlot Trotway made for a great place to setup. We were close, but not too close to the Everfree Forest and could see anything trying to get us. It was also remote enough that we wouldn't get any disgusted looks from boring traditionalists who believe that sex should only be between two consenting adults on solid ground.

They don’t know what they’re missing.

"Everything looking good over there, Stuntman?" asked Thunderlane, strapping on his flight goggles.

I replied with an upturned thumb.

He nodded and grinned. "We've got enough low level cloud clutter set up today that we should avoid too much attention from the ground, but the only way to be sure we won't be seen would be to fly over the forest edge, and avoid the most direct flight paths between here and Canterlot." Thunderlane continued, his tone all business even as his eyes had a rather lascivious look. "It's up to you two."

I looked into Flitter's lilac eyes and ran my fingers through her forelock. "I'm here on business so rather not be seen in the air today. Can we do a low-level run over the forest?"

"Sure. Ah really don't trust this weak cloud cover either," Flitter replied her wings rustling with even greater urgency, "We better hurry up and get into the air before muh wings lock up!" she told me, her eyes already starting to glaze in anticipation.

"Don't chicken out on me sis!" Cloudchaser scolded adding a wink and a nod to acknowledge her shameless pun as the others laughed good-naturedly.

"It's just a little banging, you'll be fine," Cloud Kicker added with an impish grin.

"Very funny gals," Flitter muttered to herself, equal parts excited and nervous as the moment of truth and promised rapture approached.

"Flitter, are you alright for the take-off?" asked Thunderlane with a gentler tone, recognizing her need for reassurance. Have to say, I really like the guy. Not every stallion is okay with Gentlemen, let alone willing to help one bang the sister of one his herd mares, especially here in Ponyville.

"Yes,” Flitter replied a little shortly, her nerves starting to show.

"Alright, on five everypony!" Thunderlane called out.

Even before the count hit zero, the five began to beat their wings hard, knowing from past experience they would have to generate a ton of lift to get me the necessary distance off the ground to clear the tops of the trees. Thunderlane by far had the easiest job; he would fly over our heads and allow the line between himself and Flitter to slack. He would only be required to drag while Flitter and I were getting it on. The other three were there to keep our flight stable and our tow lines from crossing so we could have our fun safely. The goal, of course, is for one or both of the participants to climax. The rider on top is in "the cockpit" — a human flight term that had already made it into pegasi lexicon — so it was Flitter's turn to join the club.

*****

We were airborne in less than five seconds, clearing the hill and soaring off over the treetops. The sun glowed bright in the sky, suspended in the same place it had been since morning, awaiting to be cast away once more to be replaced by Luna's Moon within a few hours. Having reached our cruising altitude just over the low and scattered Everfree cloud base — it’s pretty much the only place in Equestria where you can see weather happen on its own — Flitter caught up with me and we wrapped each other up. "Welcome to The Club, Flitter," I whispered into her ear before nibbling and suckling the tip of it.

Her wings stiffened immediately. That was easy; I guess she was keyed up enough just being here. "Let me help you with that." I reached both of my hands under her wings and kneaded the sensitive flesh of her flight muscles — a enormous and often overlooked pegasi erogenous zone — while leaving a trail of kisses along her neck.

"Ahhh! Ah’m ready! Ah'm going to turn," She squeaked. Now came the fun part, as I signaled for a one-eighty shift.

Despite her stiff wings, and thanks in no small part to to the four ponies pulling us, Flitter executed the turn perfectly and positioned her moist, dripping slit within easy striking distance. I grabbed her lean, muscular flank and took a taste, making her cry out immediately, She moaned as I continued my ministrations, searching for her clit. I was trying to end things quickly, so I could get to really fun part.

Tracking it down, I licked greedily until I felt her climax coming on. Her legs began to shake uncontrollably and she came hard, screaming as the orgasm ripped through her, her wings clamping down hard on her sides and mine. Above and in front of me our comrades cheered as I got a mouthful that mostly wound up coating the front of my shirt. Farewell screaming Bronson Pinchot shirt, you died for a worthy cause.

I felt a twinge of guilt as I thought about the client I was going to be seeing in mere hours. I supposed I should be saving the best for her, but I could always use a booster later.

"Flitter!" I called out to her through the rushing wind as I felt her body go slack against me.

She responded with a giddy laugh, one of liberation and overcome fear. That’s my girl!

"Flitter, you want to try a midair refueling?" I asked hopefully, but she shook her head, looking dazed but happy.

"Just hold muh Stuntman..." she purred sweetly, apparently already into the afterglow and cuddle phase.

"Maybe another time, Ah just want you to hold muh." Her voice clearly indicated that she was done for the day — she’d overcome her fears, and broken out of her shell and comfort zone a bit, so I guess that was enough for the time being.

"No problem Flitter, you were awesome today!" I gave her a reassuring pat on the rump and signaled for another one-eighty shift and to head back to Ponyville airspace. We spent the better part of an hour in each other arms nuzzling and kissing each other between the occasional glancing at the sight of Ponyville sailing past us. Feeling comfortable that her wings would work again I freed her from her harness and let her fly off behind me.

She made a couple celebratory loops in the air before settling back into my arms. "Thank yeh for that Stuntman." She stole one last kiss before flying off to go do another victory lap. She's such a sweetheart. But for myself, I decided it was time to get down from here before the gods decided to smite me with another life-threatening injury… or even worse, another disapproving look and lecture from Ever Ring.

Author's Note

I have no idea whether or not the speed required to suspend a man and a cartoon pony midair would drown out speech between said man and pony. I wasn't paying attention in science class and I appreciate whatever suspension of disbelief you're able to grant me. Thank you for flying Pegasi Airlines and don't forget to turn off all cell phones before landing lest you doom us all.